Shortly before midnight of July 5th, 1863, with his headquarters established at the Monterey House, General Judson Kilpatrick divided his cavalry force. He called upon commander of the 1st Vermont Cavalry, Lieutenant Colonel Addison Preston to cut off the head of the wagon train that just passed through MontereyPass using two 3-Inch Rifles from Pennington’s Battery. Lieutenant Colonel Preston was ordered to take local civilian Charles Buhrman as his guide to assist his troops in finding the wagon train as it crossed into Maryland via Waynesboro, Pennsylvania.
Charles Buhrman knew the area very well and suspected that upon leaving Waynesboro, the Confederate wagon train took one of two major roads. The first road led directly into Smithsburg, while the other led directly into Leitersburg. Both roads led to Hagerstown, and from there to Williamsport near the Potomac River.
The road leading from MontereyPass would take the 1st Vermont Cavalry to Raven Rock Road, and from there into Smithsburg. Heading through RavenRockPass, a few miles south of MontereyPass, Sergeant Henry Ide recalled the terror of the night. “The night was intensively dark, the rain was falling in torrents, the lightning flashed and then striking trees and rocks in our immediate vicinity.” Besides the weather, road conditions began to take a toll on many of the soldiers and their horses. Sergeant Ide continued; “The road was rough; a mere wood road over and amongst the rocks. A good many horses lost their shoes, and soon became lame, the riders would have to dismount and lead, and of course fell behind.”
As the 1stVermont descended SouthMountain through RavenRockPass, they came into Smithsburg. There was no activity or indications that a Confederate wagon train had gone through the small town. Lieutenant Colonel Preston then asked Buhrman what his opinion was of the situation. Knowing the area, Buhrman assured Lieutenant Colonel Preston that the wagon train they were looking to head off was located three miles west at Leitersburg.
Using the Smithsburg and & Leitersburg Turnpike, they began moving onto Leitersburg. The turnpike itself was a good road with several rolling hills that led to the center of Leitersburg. At around three o’clock in the morning on July 5th, the 1st Vermont Cavalry ascended up the last main hill, east of town, and intersected the rear portion of a Confederate wagon train that they were in search of. With no warning and complete surprise, the Vermonters launched their attack.
The scene became very wild as cattle, Confederate soldiers, horses, and wagons crowed the road. As soon as the revolvers and carbines cracked, several mules began running away with their wagons still attached. Some ran off the road into the ditch, turning over. Most of these wagons had wounded Confederate soldiers inside. One Union trooper recalled hearing the screams of those who were in pain. Many of the soldiers who were wounded, but sustained no life threatening injuries were hopping out of the wagons. Several of the wagon drivers were shot by the Vermonters.
Realizing that the head of the wagon train was still moving toward Hagerstown, Lieutenant Colonel Preston divided his regiment. He led the majority of his men toward Hagerstown to cut off the head before it got into Hagerstown. The other half was ordered to meet back up with Kilpatrick, with Buhrman as their escort. Preston managed to get in front of the head of the wagon train and forced it to stop. The Confederates made several attempts to recapture their wagon train, but those attempts failed.
By dawn, fearing that he was too far ahead of Kilpatrick, Lieutenant Colonel Preston ordered a halt just east of Hagerstown. With the action of Leitersburg, the 1st Vermont Cavalry captured 100 Confederate soldiers, three miles of wagons and a large herd of cattle. The Vermonters inventoried the wagons, removing all wounded men from inside. The wagons were then burned or the wooden spokes of the wheels were busted out to render them useless.
Seeing the glow to their south just before daylight, the people of Waynesboro had just had a “Fourth of July” celebration like no other. They saw the fires of the burning wagons at Leitersburg. To the east, as Kilpatrick’s cavalry descended SouthMountain, the people of Waynesboro saw the fires extending down the mountainside from MontereyPass. Shortly after daybreak, the citizens of Waynesboro saw another glow in the sky. These were the fires of those wagons burned at Ringold.
Combined, approximately nines miles worth of wagons were destroyed and roughly 1,300 Confederate prisoners were taken during the Battle of Monterey Pass and the side action at Leitersburg, Maryland. Because of these two actions, this makes the Battle of Monterey Pass, Pennsylvania’s second largest battle and the only battle to be fought on both sides.